Planning winter sailing escapes—Sailing news from the U.S. and beyond

by David Schmidt, Sail-World USA Editor on 9 Jan 2016 As winter starts to become serious in many parts of the country, it’s only natural that smart sailors start dreaming of warmer locales, crisp tradewinds, bathtub-warm waters and the fantastic winter and spring racing series that unfurl yearly throughout Florida, the Caribbean, and, finally Cuba. These regattas have historically kicked off with Key West Race Week (January 17-22, 2016) before then migrating to the Caribbean, but this year’s Conch Republic Cup (January 27-February 6) is set to offer some fantastic racing just 90 miles from Key West.

The Conch Republic Cup Key West Cuba Race Week begins with an offshore leg that takes racers from the Conch Republic across the Gulf Stream to the once forbidden (for Americans at least) island nation of Cuba. Once in Cuba, racers can look forward to some interesting buoy racing, fascinating cultural exchanges ashore with locals, great music, and plenty of parties and evening entertainment. Then, a final offshore sprint carries the fleet back to Florida.

(N.B., While the Conch Republic Cup sounds like a fantastic way to stretch out a Key West Race Week winter escape into a multi-week adventure, owners are advised to carefully research the necessary permits required to travel to Cuba and to speak with the race organizers, as there have been reports of the United States Coast Guard fining returning boats that had the wrong paperwork.)

Further south, traveling sailors fleeing winter’s icy chill can expect great Caribbean racing, starting this month with events such as the St. Thomas Yacht Club’s MLK Regatta (January 9-10), the Mount Gay Rum Round Barbados (January 16-24) and Grenada Sailing Week (January 28-February 2).

For distance racers, the Caribbean 600 (long on my regatta bucket list) kicks off on February 22 and takes racers on a truly beautiful tour of some of the world’s prettiest islands stretching from Anguilla in the north all the way to Guadeloupe in the south, with some interesting “inner triangle” course work between Antigua and Barbuda and Montserrat. By all accounts, this event is quickly becoming one of the world’s classic “middle distance” races, and its dead-of-winter start date could not be better timed for any sun- and saline-starved sailors living in North America.

For round-the-can racers, the Caribbean racing scene really gets rolling in early March when the starting guns start sounding for the annual St. Maarten Heineken Regatta (March 4-6), followed soon thereafter by the St. Thomas International Regatta (March 25-27), the BVI Spring Regatta (March 28-April 3), and Antigua Sailing Week (April 24-29). In between, there are plenty of engaging, lower-profile Caribbean events that offer plenty of sunshine, breeze, great racing and fun times ashore.

So, if you find yourself pining for the smell of sunscreen, sunbaked sailcloth, and saltwater, do yourself a favor and look into participating in one or two of these fine winter or spring regattas. Event depending, there are opportunities to charter bare boats, raceboats or fully crewed steeds, budgets and itineraries depending. Better still, of course, is to plan ahead and bring your own boat to the Caribbean’s warm waters for the winter season, but this is by no means a prerequisite to enjoying a great winter escape.

For sailors who are not interested in chartering a boat (or delivering their own vessel from the mainland) and organizing a crew, companies such as Ondeck Sailing offer for-pay crewing and training opportunities at a number of Caribbean events, allowing you to maximize your sailing time while minimizing your big-picture planning responsibilities.

Finally, sun-depraved sailors are reminded that raceboats always need extra hands, especially if its windy at the dock in the morning, so you can always try the time-honored tact of simply arriving and seeing who needs help. While this is far from a guarantee of wind and salt in your face, it sure beats a winter’s morning spent shoveling the driveway, unearthing the car, or slipping and sliding to work on icy roads.

May the four winds blow you safely home,